244: Asking Better Questions and Designing Your Ideal Day with Claire Giovino

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I think acknowledging like answers that I already have about what really does give me energy. What are the things I really do need to let go of, including relationships. What relationships do you feel energized going into during and leaving those interactions? And so bringing awareness to answers that already live inside me is a theme right now. Yeah, I love that question. What am I pretending not to know?

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Welcome back Free Timers. I am so excited to have Claire Giovino with us here today. After an extensive career in academia, she began optimizing inboxes for industry leaders, launching Inbox Done with one of her clients in 2017, she noticed that in managing his inbox it was this perpetually gnarly thing, so the two of them ended up creating a whole company around it. You've heard Yarrow on the pod before in episode 161 on inbox taming and they quickly scaled the business to 10x revenue in three years with no startup capital. So these are systems lovers after my own heart. Claire has always been a seeker, maneuvering her way through life with constant questioning and after years of growing this online business with Inbox Den, she also now seeks out her dream podcast guests at her podcast the Better Questions and she hosts her Better Question dinners nationwide. Claire, welcome to the show.

Thanks for having me Jenny.

My perpetual rant on this podcast and even in the free time book is that every time a new social media company launches, we're all handed a new inbox, essentially. So where inbox was already something gnarly and never ending 10, 15, 20 years ago, now we're all juggling 10 inboxes. It feels like even with the best systems and practices, it's still too much for any one person to handle, at least if they're running their own business. I'm curious to hear your take. Having had such a front row seat to the evolution of inboxes over these last many years, what is the state of inboxes today?

As you see it, it's still the direct line to your customer and your client. After all of these years, email is still has these high conversion rates. And you're right. Now we do have multiple inboxes with our DMs and our messages and all these different places we need to go. So I think it just requires us to be even more ruthless in what we allow into our sphere. And we know that we have these very limited resources of time and energy and attention. And with attention being the currency right now, everyone wants a little piece of it. And so I think starting by questioning like, do I actually need all of these 10 plus new inboxes just being really selective about what we're letting in and creating standard for what makes the cut in your life and then always asking that question of am I the person who should be managing this or can someone else give their attention to these multiple spaces or messages are coming in? Even just the whole concept is like kind of bizarre and so new that anyone at any time can drop a message into our space. And then now the expectation is on us to, to respond on their preferred timeline. And so we just have to kind of figure out what we're okay with, setting that expectation, management around the clients and customers and people adjust to what kind of turnaround time you want to offer. But yeah, to managing and triaging and wrangling all of those different spaces now that exist. I think it's just being really ruthless about what makes the cut in your attention sphere.

I hired my first virtual assistant around 2012 and I'm somebody that I love systems, I love operational efficiency, I love software. Still to this day, I find email to be one of the hardest things to train somebody to help with. I'm wondering your take on why it is that business owners who are otherwise resourceful, strategic, creative, how come for so many of us, our inbox continues to be this gnarly, vexing area of the business. Like it just is. So easier said than done. Even if we know we might need help in our inboxes, it can be incredibly challenging to get systems that actually work and that don't just create more work for all involved. Why is that?

There are a few reasons. I talked to a client recently where she wanted to bring in an assistant and she felt like she always had to choose between trust and tech savviness, that she thought it was always kind of miss one or the other. So I think there's just general concerns around safety and privacy. Like the inbox is such a hub and contains so many, you know, all the moving pieces of your business, usually really sensitive information at times. And so there's just a trust factor to begin with that goes deeper than just like Instagram DMs, that trust factor has to be there of letting somebody in. And how do you establish that trust for handing over the reins? And then there's this idea that my emails are special, like my case is special, and that there are cases and emails that only I know how to answer. And what I've seen over and over, and having done this so many times with so many clients, is the same types of patterns exist, no matter the industry, no matter the business model, if we can systematize and template every single inbox, and that's been proven over and over. So I think there is this idea of, yes, of course no one will serve your customer and client like you. Your unique lens and your intersection of expertise and education is what makes your offering so compelling. That is unique. But the emails itself, you know, as a lover of systems, if we break it down and really categorize what are the problems and solutions showing up in these emails, Questions being asked. We can turn a lot of emails into templates with an FAQ kind of library, or we can create if then conditional logic for if this type of email comes in, then follow these steps. So that's another reason where I see the inbox kind of being the last place where something is delegated or outsourced. And then I think there is an element of the business owner especially wanting to keep that touch point of what's happening in their business and not ever wanting to feel out of the loop. But what has happened now is it's become expected that you aren't going to always be interacting with the business owner, with the person themselves, and that you will be interacting with an assistant. So it's very normalized now that you won't be the one answering your emails. And that's what that system provides, is that buffer of time. And then you're looped in sparingly, which then gives you all this freedom and more headspace to spend time in your day doing exactly what you want to be doing.

You mentioned the trust piece and certainly there's the trust of giving somebody access to so much because email really contains Everything, especially if we're looking at a business inbox or several and personal email. What about team members or email team members responding in ways that like in the past, sometimes I'll read a reply retroactively after it's sent and I kind of cringe. You know, I think every business owner probably has that feeling at some point or another. They would have done it a little differently or the answer is a little incorrect. And what do you say to somebody who's just nervous about those kinds of things happening or even somebody having to just learn on the job how to get the tone just so at least business owners who are formerly really close to this area and myself included, there's a certain tone that I really cherish and it's hard to learn sometimes you could say warm, friendly, professional. But what does that actually mean? What does that look like? How many exclamation marks are too much? What's not enough? How do you encourage people? And how do you train your team members out of moxten to nail the tone piece of this?

We do have an extensive hiring, vetting, training process and then we have a matching process where we're really often matching for personality. As you know that so much business and managing a team is personality management. And so what we do is a big focus on drafting. So when you outsource and delegate, people think we're outsourcing and delegating tasks, but we're outsourcing and delegating decisions. So we start with really micro decisions, really low stakes decisions are the first thing to get handed over to the assistant. Where do we file this email? Can we archive this, delete it, forward it? Those like little micro decisions, once those have been clearly mastered and proven to have been learned thoroughly, then we move into the like you're saying the higher stakes things, that relationship building the rapport, your brand, because your tone is your brand. And we do that through drafting. So the first round is assistants writing how they would respond or drafts. And then you as the business owner gets to review the drafts and sign off on them and actually be the one to get sent. And you can stay in that phase for as long as you want. Some business owners or some of our clients prefer to stay in that phase indefinitely just because not having to ever write an email from scratch again is so helpful. And then they just like to be the one to hit send your preference around how much control you want to have. But really what you see take shape is as you start to make these little edits and tweaks, the assistant learns through noting the differences between the drafts that they wrote and the final email that went out. And then I totally know what you mean about that feeling. And as someone who likes to have control and had to learn how to let that go in order to have a self run and self managed business, it is just learning to be okay with 5% of mistakes and things not going perfectly how I would like for the larger vision of me being able to delegate and outsource. And I always view like the first time kind of like a little mistake or a little tone inconsistency happens. I always see as a reflection of me in my training, like okay, something must have been missed there or wasn't clear in my drafting feedback. When it happens again, that's when I'm going to have a conversation with them and that's when we're going to make sure you know it is a good personality match and that this is someone who is able to learn and adapt to the tone that is so important for our brand.

We'll be right back just after this.

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Pretty sure I asked Yarrow this. What are the most common emails that you see your clients or you reserve? Like those are the ones that they don't have an assistant draft or that they always send. Or it's important that they have their name on it and not somebody jumping in for so and so. So what's that last mile of emails really?

Again, it's that hierarchy going up to the higher stakes decisions and relationships. So they're really important relationships where maybe they're okay with a lower ticket price not being the one to directly answer those emails. But for clients or customers who are paying more, they want those clients or customers to feel like they do have access to them. So it is understandably the really important relationships or emails that are attached to really high level financial outcomes. And again, that's where the drafting works really well, where you always get to be the one to hit send. But then we're removing 98% of the work that it takes to send those emails. I would say that. And then personal too. You know, we've had many clients ask us to take over all their personal affairs, not just business, but that's pretty rare. Usually people want to stay inside their own personal inbox.

Yeah, I was wondering about that. It's like, oh, can you draft a reply to this family member? I doubt that there's too much of that happening. I know that we're talking, or at least we're starting with email. But first of all, the inbox is everything. That's what I've learned over the many years. It's not just one area of the business, it's every area of the business that it touches. But getting more efficient with email is not an end in itself. It's kind of about the bigger picture you've mentioned. It's about having an independent business, having some lifestyle freedom, having some mental space and capacity freed up because you're not just like running in the hamster wheel of replying all day. So I know you're really passionate about helping business owners design their ideal day. What is the trajectory like? I don't know. You tell me where you want to start with this. But it seems like step one is just tame the chaos of the inbox, but that eventually at least your passion, even outside of inbox then is helping people get to that real sense of freedom.

I would actually say step one is to go really big and tap into your visionary capacity of if you could spend your day however you wanted, what would that look like? And what would the parts of your business, where would they show up on a daily basis? Ideally, and that's where this question of am I the one who should be doing this? Should be asked over and over again. And we focus a lot on the how. And of course, when you have an assistant, the how is very important. Building those sops and processes to make sure everything gets done consistently and at a level that you are comfortable with. But the who is often so much more important than the how. And so constantly asking yourself. It's really similar actually to a financial audit and a budget. When you look back of how your money was spent and where it went and why it went to those places I always recommend to clients to do the same thing with their time, even if it's just for a few days. Ideally it's a whole one whole work week. But even just a few days of where your time is going and just tracking, which I know when you have like 40 different tabs up on your computer and you're jumping around to different tasks, it can feel even more daunting to kind of have this pulled back meta awareness of yourself and what you're actually doing and how you're actually filling your day. But I have seen nothing be more valuable when it comes to the relationship with your time, which again is that limited resource that we talked about, along with energy and attention of just tracking for a couple days. You can do it in 10, 15 minute blocks, whatever's easiest. And then highlighting like what actually gave you energy and what actually required your expertise in a way that fulfilled you and where you're applying that 8020 rule. So where is your 20% effort producing 80% of the results? And often that is tied to your energy. I'm very much about powering the energy. So how does your energy feel? Going into, during and leaving a task is such a good litmus test for deciding if it's something that should stay in your day. When we're envisioning and creating and designing what our ideal day would be, and then when we have that time audit, then we can look and see the circle tasks, something that you actually want to be doing long term, or the areas that you actually want to be cultivating and growing. Or maybe you are just so flooded in all the like the chaos like you've said of the inbox, all the administration kind of minutiae that there was no time in your day to do the thing that you actually want to be doing, which is maybe writing, but you don't have time because you're working more in the marketing or just answering emails. So that is always where I recommend starting. And then from there we can reverse engineer and outsource and delegate all the tasks on that list of what doesn't fit into your ideal day.

I heard this great suggestion on a podcast once, I forget who, but at the end of each day he retroactively color codes the meetings on his calendar. Red if it drained his energy, orange if it was neutral, and green if it energized him. I thought, that's so smart. So he could look back months at a time and just take that energy audit.

Like you said, really smart. I love that.

I would imagine at a meta level there was probably a really intense phase of building the company Inbox done and then you probably at some point did your own energy audit. And even having a co founder who is your former client, you had just managed his inbox so well that you turned it into a whole replicable system for other people. What was the point where you did an energy audit sort of within the scope of Inbox Den. And what did you learn about yourself? Because I know you do have your own creative projects that you've launched since then, but I'm wondering if you could just walk us through a moment where you did this.

I'm sure your listeners know when you're building anything, you wear all the hats in the beginning. And it is this really interesting balance where I think before you can delegate and outsource a role or a position, you do have to know what you're delegating and outsourcing so that you're able to train the person on it and teach them on it. That being said, I have found more and more that it's not so important that I learn all the ins and outs, say of a new platform, but just finding someone with proven expertise of that platform and building my communication and my expectation management with them and just focusing on their outcome and results. So in the beginning of a startup, yes, I was wearing all the hats, you know, every position in the company and there's just this tipping point and it's again, I'm sure many of your listeners know of where you literally don't have enough time in the day to do all the things as your business is growing. But you're also in a space of like, you don't have all of the revenue yet where you can outsource and delegate all of these different roles and different hats you're wearing. So you do have to be really selective about where you bring in that help first and then of course leveraging it to increase the revenue so you can outsource more and more of those roles. And again, it's defining exactly what hat you want to be wearing. I love kind of a blend of like operations and finance. I've always like I'm dipping in a little bit to C O O and cfo. So that's fine, you design your hat. But originally I had to wear all of the hats before I could delegate and outsource. But then in addition to that, I'm looking for areas that are not my expertise, of course to bring other people in to fill those gaps and then help them define and decide their unique strength and contribution, which is their ideal thing. Look like so that we can make sure that they are thriving in whatever their strength is and their skill set is on a daily basis. So that's why that who becomes so important. So then you can define that how in every role that you do end up delegating. So when we started the business, at first I just wanted to see if I could replicate everything I did for my co founder. So I was the one actually in all the inboxes of all the clients. And then I think I've got up to like six or seven clients that I'm doing late into the night. At the same time, I'm growing the actual business itself and realizing, okay, it's time to train. So I brought in my first three assistants, trained them, and delegated and outsourced all of the inboxes that I was personally handling. It worked great. Documenting it every step, making sure SOPs are being created. And then that freed me up to only focus on the internal side. And then that's what gave me that space to continue to develop those systems to pull people into. We have something that I love called the role description document. And so whenever anyone in a role is learning something new, I say go add this to your RD or your role description document and it builds organically their role. So it's this continually evolving thing and then we can review the role description doc on a monthly or quarterly basis and say, is this still working? Is this still something that you personally want to be handling or should we give this to someone else? Where should we add in what gaps are here? So it really is this living, breathing role that everybody is in.

We'll be right back just after this.

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I often tell people something similar. Anything I say, anything we talk about update the manager manual, but I don't have them necessarily updating the role description document. So I love that you've just given us a name for that, even an abbrev the rd that you review it regularly too. Because it's true that the roles do shift and evolve over time and I love that you do that. That just plugged in a new little piece for me that was missing like some language there in terms of operating the day to day of the business. I'm always curious about people who have co founders because I can imagine it's so beneficial and yet it is a marriage and it's probably not always easy and I personally don't know if I could do it. So I'm always curious about people who do. In the current state of inbox den, how do you and Yarrow divide up responsibilities?

So I have to be clear, said no to partnership opportunities for exactly the reason you mentioned. It can go so wrong. And I just feel so lucky that I got to work with Yarrow first in a client capacity. So I got to know him really well on that level. And because of the trust we built for a long time and that dynamic, I felt really comfortable going and raising his takes and leveling up with him. So he is very much in charge of the marketing side of things. He is very much the visionary of this business, which I love and which is needed. So on our founder calls, he'll come with 10, 15, 20 ideas and we go through. And then it's more my role has become, okay, we can pick these two to execute immediately in these ways because they are the priority and they move the needle the most for us right now based on our goals. So that combination has been amazing. Where I believe it's in the E Myth, the book, there's these three categories of visionary, manager and doer that everyone tends to fall into and you can be a hybrid of a couple. But Yarrow is like a visionary through and through and I am a manager going through. And then our assistants are very much doers on a day to day basis. They're the ones every day showing up, you know, with clients. And so that's just even another kind of archetype that has been really helpful where my managerial energy just complements his visionary energies.

Yeah, those three. That book, I joke, it took me eight years to read because I started it and I got bored. It wasn't until eight years later when I revisited I'm like, this is brilliant. And of course it's called E Myth Revisited. But only later Could I understand what he was really talking about in terms of those three hats and all the systems? And I remember initially just being like, but I don't want to be McDonald's. But just there's so much wisdom in that book. And I love hearing about the two of your roles, just what comes naturally. Tell us about the better questions because it seems like this is another big part of you that lights you up for quotes and questions and talking with brilliant people on your podcast. What inspired you to start that?

I am fascinated by change. And so that's really the theme of the podcast, is what does it take to change? And examining that space in where you are now and where you want to be, or who you are now and who you want to be, and that space between knowing and doing. And I'm sure, you know, like, I could read forever about all of these systems clicking and hacking and optimizing and business management, but it's the implementation of turning it into action, which is where it comes alive. So I've seen a lot of clients kind of living and existing in that space in between knowledge and action. And so I find that in that gap are just so many questions that we carry around with us on a daily basis, often unspoken. And so, yeah, it's a lot of conversations with people who have changed in big ways and small ways, and definitely like a therapeutic lens. I've talked to a lot of creators, a lot of psychologists, and it really is this theme of questioning, of this idea of the better your questions, the better your answers, the better your quality of life. The brain is a problem solving tool. That's how it is built. It is always going to create a problem, and so you might as well feed it a really good one. You can give it an intention before you go to bed at night, and it will work on your behalf, just setting that intention before you go to sleep. But we are constantly on a regular basis feeding our brain questions and so getting as aware as possible. For example, instead of asking, why do I keep failing? Your brain will go fetch you an answer versus what am I not seeing here? Your brain will fetch you a better answer. And so it shows up everywhere. And it's just become the same in my life, especially in working with clients. I'm sure, you know, so many of our clients have so much information and knowledge in their head and they haven't gone through this process of training someone else on how to run their business, essentially. And so we apply this high level, high quality question asking in our training for all of our assistants. And so the assistants are able to draw out every client and guide them through this process. And that's what pulls out all this information that lives in one person's head, into documentation and into SOPs. And so it's just kind of my ethos. And it shows up everywhere in the podcast. It's like the purest form of this belief I have around the importance of the questions that we ask ourselves. But it definitely shows up in the business on a daily basis as well. And the training that we do with assistants and the training that we ask clients to go through too, through this really unique process of delegating.

On the podcast website, right there at the top, you ask, what questions do you carry with you? And so I'm curious, do you have a current question to juror that you're carrying with you at the moment?

One question that keeps coming up for me is, what am I pretending not to know? I think that we have a lot of the answers already. It's both. And we have the answers. And also the point in asking questions isn't to get immediate answers, it's to voice the question, shape the question. And then the poet wrote, he says, live yourself into the answer, so in some distant day you find that you have lead your way to that answer. And so I think acknowledging, like, answers that I already have about what really does give me energy. What are the things I really do need to let go of, including relationships. What relationships do you feel energized going into during and leaving those interactions? And so bringing awareness to answers that already live inside me is a theme right now. Yeah, I love that question. What am I pretending not to know? It's so good.

I recently had a big birthday. It was my 40th. And so I did a little tea party with friends here in New York City. And I read Alice in Wonderland quotes, and I wish I could tell it verbatim. I'll have to put it in the show notes, sorry, listeners. But essentially one of them, and I saved it for the last question of a two hour tea service, was, who are you ready to stop pretending to be? And when I read it, I read the quote, and then that was my question around it, and everyone's like, whoa.

If I had started with that, people would have been too intimidated. But it was just incredible what started to open up for people of who they're ready to stop pretending to be. And your question, this one comes just before that, which is like, what am I pretending not to know? Or not that there's a linear sequence of These. But this pretending phrase is so powerful, gets us to drop some of the masks that we all wear. It's like part of being a human being to function in society. But I really love this. What a gift you've just given us.

Oh, and your tea party sounds amazing.

It was so low key. It was like, true Grandma birthday was afternoon tea. Like, no booze, no late nights, no travel. The last question, if you could give fellow business owners permission to do something differently or drop something altogether, what would it be?

The obvious answer from our conversation is their email. But I would say permission to drop even things that you're good at. Many business owners are talented in so many ways, often by necessity, because when you're building a business, you have to learn and adapt and cultivate all of these different skills. You build your business and what can happen is you often could get really good at things that actually don't bring you energy and fulfillment. And so I also love the question, is this nourishing me or depleting me? And I think we can get very distracted, especially if we're praised for something that we do well. I've seen clients and many people go down a path and trajectory for a long time just because they've received external validation on a specific skill set when it's not something that actually nourishes them or gives their energy. And I had this moment actually, was how the podcast was born, where I was doing ghost writing and I just realized, like, I don't want to write for other people and other people's voices anymore. I want to write for me. Like, this isn't a skill set that I can do it. And I was doing it well. But it wasn't one that I wanted to continue to get better at and asked myself, if I could be amazing at anything, what would it be? And it was facilitating amazing conversations and asking amazing questions. So I would say do drop things even that you are very good at if they are not taking you down a path or trajectory that really excites you and energizes and nourishes you.

Amazing. Thank you so much, Claire. It's been such a joy chatting with you. I will put the links to your podcast and inbox done in the show notes. Is there anywhere else you'd like to.

Send people now that's perfect.

Okay. I love it. Likewise, and thank you for the ample permission. This might be our first ample permission slip. Like over and above whatever we would give ourselves, you're giving to us. So thank you.

Thank you.

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